Methane → (2S)-3-phenyl-2-piperidinocarbonyloxypropionic acid benzyl ester

HRID 1290073Notes

Reaction equation

HRID 1290073 reaction equation
C.ClC([O:5][C:6](Cl)(Cl)Cl)=O.[CH2:10]([O:17][C:18](=[O:28])[C@@H:19]([OH:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCCC1.ClCCl.C(N(CC)CC)C>[CH2:10]([O:17][C:18](=[O:28])[C@@H:19]([O:27][C:6]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:5])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 8082PiperidineHCID 10426DiphosgeneHCID 10377698Benzyl (S)-(-)-2-hydroxy-3-phenylpropionate

Product 1

HCID 67660486(2S)-3-phenyl-2-piperidinocarbonyloxypropionic acid benzyl ester

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Active charcoal (30 mg) and trichloromethyl chloroformate (1.06 ml) were added to a solution of (2S)-2-hydroxy-3-phenylpropionic acid benzyl ester (3.0 g) in dry tetrahydrofuran (10 ml) and the mixture was stirred at room temperature overnight. A solution of piperidine (3.47 ml) and triethylamine (4.89 ml) in dichloromethane (10 ml) was added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Ethyl acetate (50 ml) was added and the mixture was washed with 0.01N hydrochloric acid, a saturated aqueous solution of NaHCO3 and saturated brine. The organic layer was dried over MgSO4 and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=1/9→2/8 v/v) to give 4.71 g of the title compound as a colorless oil (see Table 9).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate (50 ml) was added
  5. washthe mixture was washed with 0.01N hydrochloric acid
  6. dry with materialThe organic layer was dried over MgSO4
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=1/9→2/8 v/v)

Sources & evidence

ORD record
ord-10425509ec9846b9842db47413baef00
Source dataset
uspto-grants-1998_05
Patent number
US05750696

Reaction notes

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